The Gerry Mulligan Meets Ben Webster album is best known for its exquisite version of Billy Strayhorn's "Chelsea Bridge," but Mulligan's endearing gem of a ballad, "Tell Me When," should not be overlooked. The fact that Mulligan and Webster are so relaxed and in sync with one another on both of these tracks (as well as the other nine selections) is largely due to their friendship and having played together in Los Angeles prior to going into the studio. As Mulligan told Phil Schaap in 1990: "Ben and I were a focused, near-functioning little band. That's why it it worked and of course it's all related to our mutual esteem and musical rapport."

Jimmy Rowles' short-lived, but dark and slightly foreboding intro does not prepare the listener for Webster's luscious, buoyant recital of the winsome "Tell Me When" theme, as Mulligan plays tenderly apt obbligatos along with him. Webster's solo is generally evocative of his main influence, Coleman Hawkins, in the effervescent contours of his lines, but Ben's creamy tone is unmistakably his own. The glorious interweaving of tenor and baritone as they renegotiate the melody is unforgettably poignant and soothing. Unlike on "Chelsea Bridge," Mulligan regrettably does not take a solo, but Webster more than makes up for the omission.